Thionyl Chloride → 4'-(Benzyloxy)-3'-(1-chloro-3,3-dimethylbutyl)-2-fluoro-5-methoxy-1,1'-biphenyl

HRID 1049441Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[F:23])=[CH:11][C:10]=1[CH:24](O)[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:33])=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[F:23])=[CH:11][C:10]=1[CH:24]([Cl:33])[CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1-(4-(benzyloxy)-2′-fluoro-5′-methoxy-[1,1′-biphenyl]-3-yl)-3,3-dimethylbutan-1-ol (1.00 g) in toluene (10 mL) was added thionyl chloride (437 mg), and the mixture was stirred at 70° C. for 1 hr. The solvent was evaporated under reduced pressure to give the title compound as a crude product. This compound was used for the next step without further purification.

Workup

customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-70f9bc91334648a2ac13e714124e4c1b
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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